WHY I STOPPED: First thing's first, there's no shortage of style when you're walking around Soho in New York City. If you've never heard of Soho, no worries. It's just a stretch of several blocks in lower Manhattan that also happens to be the fashion capitol of the US. Crazy, right?

While I was out there, I took some time to walk the length of Broadway that runs through Soho. I wanted to find some street style that I could bring back with me. Looks that could push us to try something new without feeling like we're getting too crazy. That's exactly what I like about Kyle's look.

First off, this look does wonders with a mix of grays and blacks. Maybe you didn't notice it at first, but the coat he's wearing is a bomber jacket. It's just not the green variety we've seen so far this season, and I love that difference.

Bombers are clean and sleek, but Kyle's style comes across as anything but cold. That has a lot to do with the sweater he's wearing under the bomber. It's tough to see from a distance, but the sweater is a soft, black velvet mixed with an incredibly subtle, deep-gray, abstract pattern created by distressing and manipulating the velvet material. It's edgy, sure, but the warmth of the material goes a long way to making it feel inviting, even as the entire top half of his look is monochromatic.

I WOULDN'T JUDGE YOU for thinking that Kyle's pants are simple gray jeans. I'd just give you some side eye, slap you on the back, and tell you to look again. See it now? Those are suit pants. Like, nice ones. With a really incredible plaid pattern. And they take Kyle's look up three notches...minimum. Even when they rest loosely on top of his incredible boots. Throw in the beret on top, and you have a look that feels as dressy as it does casual. A perfect expression of who Kyle is: a stylist assistant running errands around Soho in the middle of a client shoot for a major magazine.

STYLE TIP CHALLENGE: It's time to break some boxes. Brace yourself. Here we go: you don't always have to be 100% dressy or 100% casual. In fact, like Kyle, you can blend garments with two distinct styles to create a look that crosses style boundaries. The key, as always, is balance. There are no strong patterns in Kyle's look. The mix of materials is already a big enough statement. If you want to do the same, keep the garments simple. Try a more causal jacket with a more formal shirt. Blend industrial boots with dress pants. Wear an f*$@& beret. Whatever you do, remember that style is all about playing with conventions to express something about yourself. Playing with conventions doesn't mean you have to go crazy; it means you can step out of the boxes you're used to and mix up your wardrobe until you've found an ensemble that makes you stop and say, "yes, this is me."

Welcome to North & Kedzie. My name is Brian Gee, and I'm inviting you to join me on my journey towards making style & culture approachable and accessible at home in Chicago and wherever else my travels may take me.